Classifications

• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
  • C08G73/02—Polyamines
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/329—Polymers modified by chemical after-treatment with organic compounds
  • C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
  • C08G65/33379—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group
  • C08G65/33386—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group cyclic
  • C08G65/33389—Polymers modified by chemical after-treatment with organic compounds containing nitrogen containing nitro group cyclic aromatic
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
  • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
  • C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
  • C08G18/46—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen
  • C08G18/4615—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen
  • C08G18/4623—Polycondensates having carboxylic or carbonic ester groups in the main chain having heteroatoms other than oxygen containing nitrogen containing primary or secondary terminal aminogroups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/48—Polyethers
  • C08G18/50—Polyethers having heteroatoms other than oxygen
  • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
  • C08G18/5024—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups
  • C08G18/5027—Polyethers having heteroatoms other than oxygen having nitrogen containing primary and/or secondary amino groups directly linked to carbocyclic groups
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/61—Polysiloxanes
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G18/00—Polymeric products of isocyanates or isothiocyanates
  • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
  • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
  • C08G18/40—High-molecular-weight compounds
  • C08G18/63—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers
  • C08G18/632—Block or graft polymers obtained by polymerising compounds having carbon-to-carbon double bonds on to polymers onto polyethers
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
  • C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
  • C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
  • C08G65/32—Polymers modified by chemical after-treatment
  • C08G65/321—Polymers modified by chemical after-treatment with inorganic compounds
  • C08G65/322—Polymers modified by chemical after-treatment with inorganic compounds containing hydrogen
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins

Definitions

• the invention relates to new compounds having terminal aminophenoxy groups, a process for their preparation and their use as structural components in the production of optionally cellular polyurethane plastics and foams.
• Terminal polyadducts containing aromatic amino groups are known in principle.
• US-PS 28 88 439 and DE-OS 17 20 646 describe the preparation of aminopolyethers by reaction of nitroaryl isocyanates with polyols and subsequent hydrogenation.
• the analogous reaction of azoaryl isocyanates with polyols also gives aromatic aminopolyethers after reduction (DE-OS 12 57 427).
• DE-OS 11 22 254 and DE-OS 16 94 152 describe a process in which NCO prepolymers are reacted with diamines which have differently reactive amino groups.
• NCO prepolymers with sulfamic acid according to DE-AS 11 55 907, with formic acid according to FR-PS 14 15 317 or with hydroxyl-containing enamines, aldimines or ketimines according to DE-OS 21 16 882 and DE-OS 25 46 536 also leads after hydrolysis or saponification to aromatic aminopolyethers, such as the thermal cleavage of urethanes from NCO prepolymers and secondary or tertiary carbinols according to DE-AS 12 70 046.
• DE-OS 29 48 419, 32 23 397, 32 23 398 describe as well as 32 23 400 different one or two-stage process for the production of aromatic polyamines by hydrolysis of NCO prepolymers in the presence of various solvent and catalyst systems.
• Aromatic amino polyethers are also obtained by reacting polyoxyalkylene polyols with p-aminobenzoic acid derivatives according to Japanese patent applications 59 053 533, 59 089 322 and 59 199 715.
• the low reactivity of the aromatic ester amines obtained in this way is disadvantageous for many purposes.
• the present invention thus relates to novel compounds of the general formula having terminal aminophenoxy groups in which 1R stands for an n-valent radical, as it stands by removing the hydroxyl groups from an n-valent polyhydroxyl compound with a molecular weight of 400-12,000, preferably 400-6,000, 2R represents a methyl group or preferably hydrogen and n is an integer from 2 to 8, preferably 2 to 4.
• the invention also relates to the use of the latter aminophen according to the invention Compounds containing oxy groups as a structural component in the production of polyurethane plastics by the isocyanate polyaddition process.
• Starting materials for the process according to the invention are (i) higher molecular weight polyhydroxyl compounds and (ii) optionally methyl-substituted nitrohalobenzenes.
• Suitable polyhydroxyl compounds (i) are preferably higher molecular weight compounds with an average molecular weight of 400-12,000, in particular 400-6,000, which have at least 1 to 9, preferably 2 to 4, reactive hydroxyl groups per mole.
• hydroxyl-containing polyacetals, polythioethers, polycarbonates, polyamides, polysiloxanes and / or polybutadienes, polyesters, polylactones and polyethers are suitable for use in polyurethane chemistry. in particular, however, polyethers bearing hydroxyl groups.
• the polyethers according to the invention which have hydroxyl groups are those of the type known per se and are known, for. B. by polymerization of epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin with itself, for. B. in the presence of BF3, or by the addition of these epoxides, optionally in a mixture or in succession, to starting components with reactive hydrogen atoms such as water, alcohols or amines, e.g. B.
• epoxides such as ethylene oxide, propylene oxide, butylene oxide, tetrahydrofuran, styrene oxide or epichlorohydrin
• BF3 BF3
• reactive hydrogen atoms such as water, alcohols or amines
• sucrose polyethers such as those e.g. B. are described in German Patent Specifications 1 176 358 and 1 064 938, come into question according to the invention. In many cases, those polyethers are preferred which are predominantly (up to 90% by weight, based on all the OH groups present in the polyether) primary OH -Groups. Also modified by vinyl polymers, polyethers such as z. B.
• polyacetals such. B. from glycols, such as di- or trio-ethylene glycol, 4,4'-dioxethoxy-diphenyl-dimethyl-methane, hexanediol and formaldehyde or by polymerization of cyclic acetals, such as. B. trioxane, producible compounds in question.
• glycols such as di- or trio-ethylene glycol, 4,4'-dioxethoxy-diphenyl-dimethyl-methane, hexanediol and formaldehyde
• polymerization of cyclic acetals such as. B. trioxane, producible compounds in question.
• Suitable polycarbonates containing hydroxyl groups are those of the type known per se, which, for. B. by reacting diols such as 1,3-propanediol, 1,4-butanediol and / or 1,6-hexanediol, di-, tri- or tetraethylene glycol or thiodiglycol with diaryl carbonates, for example diphenyl carbonate, or phosgene can be prepared (DE- B 1 694 080, 1 915 908 and 2 221 751; DE-A 2 605 024).
• Suitable polyesters from dicarboxylic acids and diols are those from adipic acid and isophthalic acid and straight-chain and / or branched diols, as are lactone polyesters, preferably based on caprolactan and starter diols.
• Polyhydroxyl compounds already containing urethane or urea groups and also modified natural polyols can also be used. Addition products of alkylene oxides on phenol-formaldehyde resins or also on urea-formaldehyde resins can also be used according to the invention. It is also possible e.g. B. according to DE-A 2 559 372, to introduce amide groups into the polyhydroxy compounds.
• polyhydroxyl compounds in which high molecular weight polyadducts or polycondensates or polymers are present in finely dispersed or dissolved form.
• Such polyhydroxyl compounds are e.g. B. obtained when polyaddition reactions (z. B. reactions between polyisocyanates and amino-functional compounds) or polycondensation reactions (z. B. between formaldehyde and phenols and / or amines) in situ in the above-mentioned, hydroxyl-containing compounds .
• Such methods are for example in the DE-B 1 168 075 and 1 260 142, and DE-A 2 324 134, 2 423 984, 2 512 385, 2 513 815, 2 550 796, 2 550 797, 2 550 833, 2 550 862, 2 633 293 and 2,639,254.
• polyhydroxyl compounds such as z. B. by polymerization of styrene and acrylonitrile in the presence of polyethers (US Pat. No. 3,383,351, 3,304,273, 3,523,093, 3,110,695, DE-B 1,152,536) or polycarbonate polyols (DE-PS 1,769,795, US -PS 3 637 909) are obtained are suitable for the process according to the invention.
• plastics When using polyether polyols which have been modified according to DE-A 2 442 101, 2 644 922 and 2 646 141 by graft polymerization with vinylphosphonic acid esters and optionally (meth) acrylonitrile, (meth) acrylamide or OH-functional (meth) acrylic acid esters, plastics are obtained of special flame retardancy.
• modified polyhydroxyl compounds of the type mentioned above gives rise to starting components which, in the polyisocyanate polyaddition process, in many cases result in polyurethane plastics with significantly improved mechanical properties.
• Suitable, albeit less preferred, polyhydroxy components (i) are also organofunctional polysil oxanes which have two terminal groups and structural units of the formula -O-Si (R) 2- which are reactive toward isocyanate groups, in which formula R represents a C1-C4-alkyl or a phenyl radical, but preferably a methyl radical.
• suitable starting materials are both the pure polysiloxanes which are known per se and have terminal organofunctional groups and the terminal organofunctional siloxanepolyoxyalkylene copolymers which are known per se.
• organopolysiloxanes which are particularly preferred according to the invention correspond to the general formula
• the starting materials (ii) which are suitable according to the invention include, where appropriate, methyl-substituted halonitrobenzenes of the general formula for which 2R represents hydrogen or a methyl group, preferably hydrogen, X represents fluorine or preferably chlorine, and in which the halogen and nitro substituents are preferably arranged ortho or para to one another.
• Particularly preferred starting materials (ii) are 2-nitrochlorobenzene or 4-nitrochlorobenzene.
• alkaline compounds which are required for the reaction of the polyhydroxyl compounds (i) with the halonitrobenzenes (ii) are metal hydrides, metal alkoxides and preferably metal hydroxides. Sodium hydroxide and potassium hydroxide are particularly preferred.
• the starting materials (ii), based on component (i), can be used both in a stoichiometric amount and in excess or deficit.
• Component (ii) is preferably dimensioned such that 1 to 1.5 mol of component (ii) is present per mole of hydroxyl groups of component (i).
• the hydrogen halide released in the reaction can be bound by adding metal hydrides, metal alkoxides and metal hydroxides. The amount is at least such that it is sufficient to neutralize the hydrogen chloride that is split off. They are particularly preferably used in an amount such that 1 to 3 mole base equivalents are available per mole of hydroxyl groups.
• Step a) of the process according to the invention is carried out in bulk or expediently in an organic solvent, if appropriate in the presence of a phase transfer catalyst.
• the reactants can be present in a homogeneous phase or in two phases, dissolved, emulsified or suspended.
• Suitable organic solvents are for example: benzene, toluene, xylene, chlorobenzene, dichlorobenzene, trichlorobenzene, diethyl ether, diisopropyl ether, tert-butyl methyl ether, tetrahydrofuran, dioxane, ethylene glycol dimethyl ether, Essigester, acetone, methyl ethyl ketone, acetonitrile, furfural, methylene chloride, chloroform, trichlorethylene, tetrachlorethylene , Nitromethane, nitropropane.
• Polar aprotic solvents are preferred such as, for example, dimethylformamide, dimethylacetamide, N-methylpyrrolidone, tetramethylurea, N-methylcaprolactam, dimethylsulfoxide, tetramethylene sulfone, hexamethylenephosphoric triamide, etc.
• Dimethylformamide, dimethylsulfoxide and N-methylpyrrolidone are very particularly preferred.
• the amount of the solvent is generally such that it is sufficient to clearly dissolve the starting materials (i) and (ii). In practice, this means that the solvents are generally used in an amount of 50 to 1,000, preferably 100 to 500 parts by weight of solvent per 100 parts by weight of the mixture of components (i) and (ii).
• a phase transfer catalyst Such catalysts are e.g. B. in EV and SS Dehmlow, Phase Transfer Catalysis, 2nd edition, Verlag Chemie 1983.
• Suitable catalysts are quaternary ammonium or phosphonium salts of the formula in which Z represents nitrogen or phosphorus, R ′, R ⁇ , R ⁇ and R ⁇ _ represent the same or different radicals and are alkyl groups having 1 to 18 carbon atoms, where one of the radicals can also represent an araliphatic radical having 7 to 15 carbon atoms, and the sum of Carbon atoms of the four radicals is preferably 12 to 31.
• Typical examples of suitable catalysts are N-benzyl-N, N, N-triethylammonium chloride or bromide, N-benzyl-N-dodecyl-N, N-dimethylammonium chloride or bromide, N, N, N, N-tetra -n-hexylammonium chloride or bromide, N-benzyl-N, N, N-tri-n-octylammonium chloride or bromide or the phosphonium salts corresponding to these ammonium salts.
• the quaternary ammonium or phosphonium salts mentioned by way of example are preferably carried out in bulk or in the form of their aqueous solutions (for example with a solids content of 30 to 60% by weight) and preferably in an amount of 1 to 10 mol% when carrying out the process according to the invention. , based on the number of moles of hydroxyl groups used.
• Stage a) of the process according to the invention is generally carried out at 10 to 100 ° C., preferably at 20 to 60 ° C., with overpressure, underpressure or expediently without pressure, continuously or batchwise.
• the residence time is generally 0.5 to 24 hours; 0.5 to 8 hours are preferred.
• stage a) of the process according to the invention one can proceed, for example, by initially introducing the starting materials and, if appropriate, the phase transfer catalyst in the solvent selected, and the base in dissolved or suspended form, preferably in solid, as finely ground as possible, with stirring, if appropriate with Cooling is added in portions or continuously.
• the mixture is subsequently stirred at room temperature or, if appropriate, at an elevated temperature until IR conversion shows that the hydroxyl groups initially present are completely converted and / or that starting material (ii) can no longer be detected by thin layer or gas chromatography.
• the nitrophenoxy adducts are worked up in a manner known per se.
• the reaction mixture is expediently diluted with an inert solvent which is not miscible with water and washed with water or brine neutral, distilled off the solvents, if necessary, in vacuo and dried in vacuo.
• the reaction mixture can also be neutralized by treatment with CO2.
• suitable inert solvents are toluene, methylene chloride, chlorobenzene, dichlorobenzene, 1,2-dichloroethane, trichlorethylene.
• stage a In principle conceivable, but less preferred, would also be a procedure which consists in feeding the reaction mixture obtained in stage a) directly to stage b), if appropriate after neutralizing the excess alkali metal hydroxide without intermediate isolation.
• the compounds containing terminal nitrophenoxy groups obtained in stage a) of the process according to the invention are converted into the corresponding polyamines in stage b) in a manner known per se by reduction with nascent or catalytic hydrogen, for example by means of Raney nickel or palladium on carbon.
• the hydrogenation can be carried out in the presence or absence of inert solvents at 20-120 ° C and a pressure of 20 to 80 bar.
• Suitable solvents are, for example, methanol, ethanol, i-propanol, toluene, DMF and others Methanol.
• the diamines are obtained as a distillation residue during the removal of the solvent by distillation and can be used for the production of polyurethane plastics without further purification steps.
• the polyamines according to the invention obtained after working up are generally brownish-colored products and are distinguished from the previously known aromatic aminopolyethers by their substantially lower viscosity.
• functional groups already present in the underlying polyhydroxyl compounds such as, for example, B. ether and / or thioether and / or dialkylsiloxane and / or carbonate groups and / or residues of polybutadienes only a number of ether groups corresponding to their functionality.
• the aromatic polyamines according to the invention are suitable as reactants for optionally blocked polyisocyanates in the production of polyurethanes (polyurethane ureas), optionally cellular polyurethane plastics or polyurethane foams, where appropriate also with other low molecular weight (molecular weight 32 to 399) and / or higher molecular weight (molecular weight 400 to approx. 12,000 compounds with groups reactive toward isocyanates can be combined.
• suitable starting components for the production of polyurethane plastics are described, for example, in DE-A 2 302 564, DE-A 2 432 764 (US Pat. No.
• the polyamines according to the invention are particularly suitable for use in combination with solid polyisocyanates.
• these components can be used to produce reaction systems which can be stored for as long as required at RT or, if appropriate, at elevated temperature and which cure only when exposed to high temperatures.
• Such systems are generally referred to as one-component systems.
• Suitable solid polyisocyanates are, for example, dimeric 2,4-diisocyanatotoluene (TT) or 3,3'-dimethyl-4,4'-diisocyanato-diphenylurea (TDIH).
• polyurethane (urea) by means of the polyamines produced according to the invention is also the subject of the present invention.
• Your application can e.g. B. for elastomers, coatings, threads in the application from melts, solutions, dispersions or as a reactive component mixture.
• Further uses of the polyamines produced according to the invention are e.g. B. coupling components for diazo dyes, hardeners for epoxy and phenolic resins, and all other known reactions of amines such as amide or imide formation and others.
• Example 2a Analogously to Example 1 b, 3,000 g (1.34 mol) of nitrophenoxy adduct according to Example 2a in 11 l of methanol are hydrogenated in the presence of 450 g of Raney nickel. Yield: 2,748 g (94% of theory) Viscosity: 1,020 mPa.s / 25 ° C (dark oil) Amine number: 56
• Example 1 b Analogously to Example 1 b, 530 g (0.16 mol) of nitrophenoxy adduct according to Example 3a in 1,500 ml of methanol are hydrogenated in the presence of 80 g of Raney nickel: Yield: 469 g (91% of theory) Viscosity: 1450 mPa's / 25 ° C (dark oil) Amine number: 46
• Example 4 a Analogously to Example 1 b, 500 g (0.3 mol) of nitrophenoxy adduct according to Example 4 a are hydrogenated in 1,600 ml of methanol in the presence of 75 g of Raney nickel. Yield: 429 g (89% of theory) Viscosity: 640 mPa.s / 50 ° C (brownish wax at 25 ° C) Amine number: 68
• Example 1b Analogously to Example 1b, 670 g (0.54 mol) of nitrophen Oxyaddukt hydrogenated according to Example 5 a in 1,400 ml of methanol in the presence of 100 g of Raney nickel. Yield: 586 g (91% of theory) Viscosity: 1,650 mPa.s / 25 ° C (dark oil) Amine number: 98
• Example I Analogously to Example I, a reaction mixture is first prepared, which must be processed in this form within 2 to 3 minutes.
• a reaction mixture is first prepared, which must be processed in this form within 2 to 3 minutes.
• 0.2 - 0.4 g of 3,3'-dimethyl-4,4'-diamino-dicyclohexylmethane (Laromin C) the watering or pot life of the reaction system described can be extended considerably and thus be adapted to practical requirements.
• the reaction systems obtained in this way can also be increased if necessary Temperature (approx. 50 - 60 ° C) can be processed for up to several days.
• a highly elastic polyurethane elastomer is obtained with the property level given for Example I.
• Example II Analogously to Example II, 200 g of the aminopolyether having an amine number of 56 and 36.4 g of finely ground 3,3'-dimethyl-4,4'-diisocyanatodiphenylurea (TDIH: reaction product of 2,4-diisocyanatotoluene (TDI) and 1 mol H2O, NCO content 24.3%) of the average grain size 10 - 30 ⁇ implemented.
• TMA thermomechanical analysis
• Example II Analogously to Example II, 200 g of the aminopolyether of amine number 102 described in Example 1b are reacted with 66.5 g of 3,3'-dimethyl-4,4'-diisocyanatodiphenylurea.
• the mechanical properties of the highly elastic polyurethane elastomer thus obtained are given in Table 1.
• Example II Analogously to Example II, 200 g of the aminopolyether of amine number 98 mentioned in Example 5b are reacted with 63.6 g of 3,3'-dimethyl-4,4'-diisocyanato-diphenylurea.
• the mechanical properties of the highly elastic polyurethane elastomer thus obtained are given in Table 1.

Landscapes

• Chemical & Material Sciences (AREA)
• Health & Medical Sciences (AREA)
• Chemical Kinetics & Catalysis (AREA)
• Medicinal Chemistry (AREA)
• Polymers & Plastics (AREA)
• Organic Chemistry (AREA)
• General Chemical & Material Sciences (AREA)
• Inorganic Chemistry (AREA)
• Polyurethanes Or Polyureas (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Polyethers (AREA)

Applications Claiming Priority (2)

Publications (2)

Family

ID=6326273

Family Applications (1)

Country Status (10)

Cited By (10)

Families Citing this family (5)

Family Cites Families (28)

• 1987
  • 1987-04-25 DE DE19873713858 patent/DE3713858A1/de not_active Withdrawn
• 1988
  • 1988-04-05 AU AU14323/88A patent/AU1432388A/en not_active Abandoned
  • 1988-04-14 EP EP88105932A patent/EP0288825A3/fr not_active Withdrawn
  • 1988-04-18 MX MX1115588A patent/MX11155A/es unknown
  • 1988-04-22 ZA ZA882847A patent/ZA882847B/xx unknown
  • 1988-04-22 DD DD88315014A patent/DD274035A5/de not_active IP Right Cessation
  • 1988-04-22 BR BR8801955A patent/BR8801955A/pt unknown
  • 1988-04-23 KR KR1019880004612A patent/KR880012671A/ko not_active Ceased
  • 1988-04-23 JP JP63099357A patent/JPS63280735A/ja active Pending
• 1990
  • 1990-07-27 US US07/558,947 patent/US5091582A/en not_active Expired - Fee Related

Also Published As

Similar Documents

Legal Events